The antifungal and insecticidal properties of carbinoloazoles are well documented in the patent literature.
U.S. Patent No. 4,689,337, issued to Bushnell et al. on Aug. 25, 1987, GB 2,156,807A, and European Patent No. 0 158 448, issued to Bushnell et al. on Oct. 16, 1985, discloses, among others, compounds of the formula: ##STR2## wherein
R.sup.1 is hydrogen, alkyl of up to six carbon atoms or carboxylic acyl of up to ten carbon atoms; and
X, Y and Z are each selected from halo, CHF.sub.2,
CF.sub.3, OCHF.sub.2 and OCF.sub.3, and Z may also be H. The compounds are disclosed as having both fungicidal and insecticidal activity.
German Patent No. DE 29 20 375, issued to Regel et al. on Nov. 20, 1980, discloses fungicides of the formula: ##STR3## wherein
R is optionally substituted phenyl, naphthyl or tetrahydronaphthyl;
R.sup.1 is optionally substituted phenyl or cycloalkyl;
R.sup.2 is hydrogen, or R.sub.1 and R.sub.2 together, in the ortho position relative to each other, denote an optionally substituted multimembered methylene bridge, or together with the phenyl ring denote naphthyl;
R.sup.3 is halogen, alkyl, alkoxy, or haloalkyl; n is 0, 1, 2 or 3; and m is 0 or 1.
U.S. Pat. No. 4,239,765, issued to Regel et al. on Dec. 16, 1980, describes antimycotic compounds including those of the formula: ##STR4## wherein R is an optionally substituted phenyl, benzyl, naphthyl, naphthylmethyl, tetrahydronaphthyl, or tetrahydronaphthylmethyl;
R.sup.1 is halogen or alkyl; and PA1 n is 0, 1, or 2. PA1 R.sup.1 is optionally substituted phenyl or cycloalkyl; PA1 R.sup.2 is hydrogen, or R.sub.1 and R.sub.2 together, in the ortho position relative to each other, denote an optionally substituted multimembered methylene bridge, or together with the phenyl ring denote naphthyl; PA1 R.sup.3 is halogen, alkyl, alkoxy, or haloalkyl; and PA1 n is 0, 1, 2 or 3. PA1 R.sup.5 is hydrogen or C.sub.1 to C.sub.3 alkyl; PA1 n is 0 or 1; PA1 R.sup.2 is hydrogen or C.sub.1 to C.sub.8 alkyl; PA1 Y is independently hydrogen, halogen, nitro, C.sub.1 to C.sub.4 alkyl, C.sub.1 to C.sub.4 alkoxy, unsubstituted amino or methyl- or ethylamino; and PA1 n is 1 or 2. PA1 R.sup.2 is phenyl, phenyl mono- to trisubstituted by halogen, C.sub.1 to C.sub.3 haloalkyl, nitro, C.sub.1 to C.sub.3 alkoxy, C.sub.1 to C.sub.8 alkyl and/or cyano, or phenyl substituted by phenyl or phenoxy, or it is C.sub.1 to C.sub.10 alkyl, C.sub.3 to C.sub.8 cycloalkyl or C.sub.3 to C.sub.8 -cycloalkyl-(C.sub.1 to C.sub.4 alkyl); PA1 R.sup.3 is C.sub.1 to C.sub.12 alkyl, C.sub.2 to C.sub.4 alkenyl, C.sub.3 to C.sub.4 alkynyl, benzyl, or benzyl mono- or disubstituted by halogen, nitro and/or C.sub.1 to C.sub.3 alkyl; and PA1 R.sub.4 is an azole group, including acid addition salts thereof, quaternary azolium salts, and metal complexes. PA1 R.sup.1 is H, OH or OCH.sub.2 R.sup.5 ; PA1 R.sup.2 is H or ##STR12## R.sup.5 is vinyl, thienyl, halothienyl or ##STR13## and R.sup.3, R.sup.4, R.sup.6, R.sup.7, R.sup.8 and R.sup.9 are independently H, OCH.sub.3, halogen, CF.sub.3, or NO.sub.2, or a PA1 Y is halogen, alkyl, haloalkyl, alkoxy, alkylthio, nitro, cyano or optionally substituted phenyl; and PA1 m and n are independently 0, 1, 2 or 3. PA1 R is dibenzothienyl or p-R.sup.5 -S-phenyl; PA1 R.sup.5 is phenyl, benzyl or akly; and PA1 n is 1, 2 or 3. PA1 R.sup.1 and R.sup.2 independently are H, F, PA1 Cl, Br, CH.sub.3, CF.sub.3 or S(O).sub.n R.sup.3 where PA1 n is 0, 1 or 2 and R.sup.3 is alkyl or PA1 1-4 carbon atoms; PA1 R.sup.4 is H or alkyl of 1-4 carbon atoms with the proviso that R.sup.4 is H when m is 2 or 3; and PA1 m is 1 to 3. PA1 (1) m is 1 and R.sup.4 is CH.sub.3 ; and/or PA1 (2) R.sup.1 and R.sup.2 are both 4-Cl or 4-F. PA1 (1) 1,1-bis(4-chlorophenyl)-2-(1-imidazolyl)propanol PA1 (2) 1,1-bis(4-fluorophenyl)-2-(1-imidazolyl)propanol.
U.S. Pat. No. 4,301,166, issued to Regel et al. on Nov. 17, 1981, discloses antimycotic compounds of the formula: ##STR5## wherein R is optionally substituted phenyl, naphthyl, or tetrahydronaphthyl;
U.S. Pat. No. 4,480,114, issued to Regel on Oct. 30, 1984, discloses a process for the preparation of compounds of U.S. Pat. 4,301,166.
U.S. Pat. No. 4,358,458, issued to Scharwachter et al. on Nov. 9, 1982, claims compounds of the formula; ##STR6## wherein R.sup.1, R.sup.2, R.sup.3 and R.sup.4 may be independently hydrogen, halogen, C.sub.1 to C.sub.4 alkyl or C.sub.1 to C.sub.4 alkoxy;
and pharmaceutically acceptable salts thereof. These compounds are claimed as useful for treatment of infections caused by fungi and yeasts.
U.S. Pat. No. 4,413,003, issued to Miller et al. on Nov. 1, 1983, discloses agricultural fungicides of the formula: ##STR7## wherein Z is an aryl or substituted aryl; and R.sup.1, R.sup.2 and R.sup.3 are independently hydrogen, cyano, alkyl, cycloakly, alkenyl, cycloalkenyl,
alkynyl, aryl, or substituted aryl. U.S. Pat. No. 4,414,210, issued to Miller et al. on Nov. 8, 1983, discloses agricultural fungicides of the formula: ##STR8## wherein W is a 1- or 4-(1,2,4-triazole); and Z, R.sup.1, R.sup.2 and R.sup.3 are the same as above for U.S. Pat. No. 4,413,003.
U.S. Pat. No. 4,472,415, issued to Worthington et al. Sept. 18, 1984, discloses triazoles of the formula: ##STR9## wherein R.sup.1 is hydrogen, C.sub.1 to C.sub.8 akly, benzyl, or benzyl substituted with halogen, C.sub.1 to C.sub.4 alkyl, nitro, trifluoromethyl, cyano, methoxy, ethoxy, phenyl, or methylenedioxy;
These compounds are claimed as agricultural fungicides.
U.K. Patent No. GB 2 110 684 A, issued to Nyfeler et al. on June 22, 1983, discloses compounds of the formula: ##STR10## wherein R.sub.1 is phenyl, phenyl mono- to trisubstituted by halogen, C.sub.1 to C.sub.3 haloalkyl, nitro, C.sub.1 to C.sub.3 alkoxy, C.sub.1 to C.sub.8 alkyl and/or cyano, or phenyl substituted by phenyl or phenoxy, naphthyl or naphthyl mono- or disubtituted by halogen, nitro and/or C.sub.1 to C.sub.3 aklyl, benzyl, or benzyl mono- or disubstituted by halogen, nitro, and/or C.sub.1 to C.sub.3 alkyl;
These compounds are diclosed as novel agricultural fungicides.
European Patent No. 0 165 783, issued to Hirsch et al. on Dec. 27, 1985, discloses compounds of the formula: ##STR11## wherein n is 1 or 2;
pharmaceutically acceptable salt thereof.
These compounds are disclosed as aromatase inhibitors for treatment and prevention of estrogen-dependent diseases.
Australian Patent No. AU-A1-68 982/81, issued to Boshagen et al. on Oct. 8, 1981, discloses, among others, compounds of the formula: ##STR14## wherein X is halogen, alkyl, haloalkyl, alkoxy, alkylthio, nitro, or cyano;
The compounds are disclosed as antimycotic agents, and their synthesis is claimed from carbinols of the formula: ##STR15## wherein X, Y, m and n are the same as above.
U.S. Pat. No. 4,285,961, issued to Prucher et al. on Aug. 25, 1981, is a patent describing various pharmacological preperties, including an antiphlogistic effect, of basic thioethers. Among the compounds disclosed are compounds of the formula: ##STR16## wherein R.sup.3 is phenyl;
U.S. Pat. No. 4,569,935, issued to Rosenberg et al. on Feb. 11, 1986, describes the use of ketoconazole in the treatment of psoriasis in humans.
None of the above-mentioned references suggests the antiinflammatory utility of the compounds of this invention.